What: A man in his early to mid 30s has hit a rut in his personal and professional life. His college sweetheart dumped him three years after graduation and since his mid 20s he has unsuccessfully played the dating game, his longest new relationship since the break-up lasting a couple of months. Professionally he has hit a ceiling where his income means he is well-off but not truly wealthy. To make matters worse, his five year younger brother - the darling of the rest of the family - outshines his older sibling in nearly everything he does. His start-up company was sold for an eight figure sum before he turned 26. He has since started up a second venture which is equally successful. He is engaged and set to marry his long-term, gorgeous girlfriend. Now our protagonist has received the invitation to his brothers wedding. He is horrified to show up at the family gathering without a date, yet he is currently without a girlfriend. Desperate, he contacts the escort he had spent a few nights with in the past six months and offers her a lump sum of cash if she agrees to join him for the three day wedding festivities in California and pretends to be his new girlfriend.

Where: The nuptials will be held in the Napa Valley

When: This game should encompass the following events: the hiring of the escort, their traveling to the wedding venue, the meeting with the family and friends, the rehearsal dinner, the actual wedding party.

Extra info: I see this game as a reinterpretation of "Pretty Woman", though perhaps less corny. But real feelings developing between client and prostitute are something I'd like to explore. I would also add some complications (like one of the wedding guests perhaps recognizing my character from when he hired her).